I want my shirt to be closed as much in the least number of buttonings. Buttoning somewhere near the top or bottom first (which lead to the second buttoning being somewhere on the other end with really high probability) has a high chance of being picked, buttoning somewhere near the middle has a lower probability (it may give the best closure for the first button, but all second buttonings will be worse than picking top & bottom). After the second or third button (given fewer than 8 buttons in total), the heuristic falls flat and it becomes a random process.

Is there a name for this type of process? The closest I can think of is poisson disc sampling, but that's a stretch.

Probably starting three or four buttons down from the collar (slightly above 'breast' height, despite neither manboobs nor prominant pecs), I then make my way down, hopeful to discover that the bottom aligns when reached (shuffling back upwards if I discover such an error). This leaves me with an unbuttoned 'V neck', not displaying so much of my manly (well, hairy!) chest, but definitely with a casual statement to it.

Should I be destined to don a tie (or even a bow-tie, assuming I can still muster the muscle-memory needed to knot it!) I shall address the remaining buttons only just prior to that part of the process, V-base on upwards. Otherwise, I leave full-buttoning only for "shoulda woulda coulda brung a tie, but didn't" situations where I emulate respectability with the fully buttoned collar as if wearing a(n invisible) tie.

Depends. If it’s a shirt that needs to be buttoned all the way, top to bottom (obviously leaving the very top button (on the collar) either unbottoned entirely or for last if I have too wear a tie). If it’s like a Hawaiian shirt that only has buttons halfway, bottom to top.